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GC- MS Analysis of Ring and Side Chain Regioismoers of Ethoxyphenethylamines

NCJ Number
Journal of Chromatographic Science Volume: 46 Dated: 2008 Pages: 671-679
T. Awad; J. DeRuiter; C. R. Clark
Date Published
9 pages

This article reports on a project that determined mass spectral differentiation of 3,4- methylenedioxymethamphetamine (3,4-MDMA), a controlled drug, and its 2,3-regioisomer from the ring substituted ethoxyphenethylamines is possible after formation of the perfluoroacyl derivatives, pentafluoropropionamides (PFPA), and heptafluorobutyrylamides (HFBA). 


The ring substituted ethoxyphenethylamines constitute a unique set of compounds having an isobaric relationship with 3,4-MDMA. These isomeric forms of the 2-, 3-, and 4-ethoxy phenethylamines have mass spectra essentially equivalent to 3,4-MDMA; all have molecular weight of 193 and major fragment ions in their electron ionization mass spectra at m/z 58 and 135/136. All the side chain regioisomers of 2-ethoxy phenethylamine having equivalent mass spectra to 3,4-MDMA were synthesized and compared via gas chromatography—mass spectrometry to 2,3- and 3,4- methylenedioxymethamphetamine. The mass spectra for the perfluoroacyl derivatives of the primary and secondary amine regioisomers were significantly individualized, and the side chain regioisomers yielded unique hydrocarbon fragment ions at m/z 148, 162, and 176. Additionally, the substituted ethoxymethamphetamines were distinguished from the methylenedioxymethamphet-amines via the presence of the m/z 107 ion. Gas chromatographic separation on relatively non-polar stationary phases successfully resolved these derivatives. (publisher abstract modified)